title: Bifunctional primary amine-thiourea-TfOH (BPAT·TfOH) as a chiral phase-transfer catalyst: the asymmetric synthesis of dihydropyrimidines.
abstract: An enantioselective Biginelli reaction has been developed by using a bifunctional primary amine-thiourea-TfOH (BPAT·TfOH) as a chiral phase-transfer catalyst and t-BuNH(2)·TFA as an additive in saturated brine at room temperature. The corresponding dihydropyrimidines were obtained in moderate-to-good yields with up to 99% ee under mild conditions. A plausible transition state has been proposed to explain the origin of the activation and the asymmetric induction.
authors.affiliation: State Key Laboratory and Institute of Elemento-Organic Chemistry, Nankai University, Tianjin, 300071, China.
authors.forename: Yangyun
authors.initials: Y
authors.lastname: Wang
authors.forename: Jipan
authors.initials: J
authors.lastname: Yu
authors.forename: Zhiwei
authors.initials: Z
authors.lastname: Miao
authors.forename: Ruyu
authors.initials: R
authors.lastname: Chen
mesh_terms: D000588:Amines / Q000737:chemistry*; D002384:Catalysis; D006865:Hydrogenation; D015394:Molecular Structure; D011743:Pyrimidines / Q000138:chemical synthesis*; D013237:Stereoisomerism; D013890:Thiourea / Q000737:chemistry*; D014269:Trifluoroacetic Acid / Q000737:chemistry*
chemical_list: D000588:Amines; D011743:Pyrimidines; D014269:Trifluoroacetic Acid; D013890:Thiourea; C030986:pyrimidine